Travel Planning Part 4: When to Book What

When to book what may be the most frequently asked question for the process of travel planning. Rightfully so as it can make or break a trip. With full honesty, I’m not sure there’s ever the “perfect time” to book parts of your trip. I’ve seen great deals to be made by booking far in advance, I’ve seen good last minute deals and on the flip side, I’ve missed out on being able to do what I wanted to because I waited to long to book. So it’s a bit of a mixed bag and I can’t say there is one exact answer for the “when to book what” — I know this isn’t the answer you probably came for, but keep reading!

What I will say is that over the years, booking far in advance has never hurt. There’s an order to the madness, and so I’ll share a bit of how I like to handle each of the categories for booking. Take a peak at step 4 of the planning process…

*p.s You can find the full travel planning series here:

Part 1: How I find My Inspiration
Part 2: How I Decide Where to Travel to
Part 3: Planning the Itinerary
Part 4: When to Book What
Part 5: Tips for on Ground

Travel Planning Part 4: When to Book What

Quick Note

At this stage in the planning process, you should have a final itinerary and I always keep it open when I start to book. I cross reference dates and locations as I make the biggest purchase decisions for the trip. I take a peak over notes, like if I saw that one of the hotels have limited availability, I’ll go in and get that booked immediately.

Flights

• The big ticket, especially when it comes to international flights. I always book this first and if using points, we often book the big round trip flights around 4-6 months in advance. For international, I recommend 2-4 months, especially if you know your itinerary and can book early.
• For hopper flights, say between cities in Europe, I will book these at the same time as my international flight. Especially during peak season, the flights between hubs can sell out.
• For booking, I always recommend booking direct with the airline. Booking third party presents a variety of issues when it comes to delayed flights and cancellations.
• If one thing goes a long way in air travel, it’s loyalty. I’m a huge believer in sticking with one airline if possible to build status, contain miles with the same company, and be able to utilize it for upgrades and future bookings. I chose Star Alliance since United’s hub is SFO and their miles can be used on other airlines in Star Alliance like Eva Air, Air Canada, and more.
• Yes it’s true, there are major deals to be had with flights and it takes a bit of work to get them. Booking certain days like Tuesday, have historically shown to be the best time. I also set Google Alerts for flights if I’m trying to scope out the best flight.
• I’ll search Kayak to get an idea of competing rates — sometimes flight prices can range, so it’s good to know what else is out there. You can also see if you’ll save some money by flying on say a Wednesday instead of a Thursday.
• When it comes to picking a day/time for flying, I always try to fly before 9 am (less chance of a delayed flight from an inbound aircraft) and I avoid weekend travel at all costs.

Accommodations

• When it comes to hotels, it completely depends the destination and how badly you want to stay at a hotel. I’ve found that I book my hotels/accommodations the same day I book my flights.
• For small, boutique hotels, like the ryokan we stayed at in Tsumago, Japan, we booked almost 4 months advance and got the last room. The smaller the hotel, the chances it will book up sooner. I recommend booking in those hotels if they’re a top priority for your itinerary.
• Now there are always the last minute stays, so often I’ll check Hotel Tonight if I need to book something the week of.
• For luxury hotels, I like to use Kiwi Collection as there are perks like upgraded room categories, early check in, and more. They’ve also heavily vetted each hotel listed on their site, so I know it’s hard to go wrong.
• For Airbnbs, if I find one I like, I’ll lock it in immediately. The cancellation policy is helpful, so I keep that in mind when I book. For some destinations, when the inventory is low, they’ll have a notification at the top of the percent of homes left for booking, which is great to note. (use this link for $40 off your first Airbnb stay).
• For pricing, I will check booking.com to see the best rates and what is offered. I’ve seen it more often than not that when you book direct with the hotel, they give more with the rate like breakfast. One perk I like about Booking.com is that a lot of the bookings can be cancelled pretty close up to date, so if I’m not sold on a place, sometimes I’ll book it in as a back up.

Trains, Transportation, & Transfers

• I book all of my transportation usually within the month of travel. I’ll lock in my rental car, I’ll book trains, and I always book a transfer for arrival.
• For train travel, it’s good to know that some months can be impacted and it’s important to book in advance in Europe. I’ll use RailEurope to book my tickets in advance.
• For on arrival transfers, I use a service called Mozio to book. It’s a great vendor for a range of transfers (group to private) and find the pricing to be fair. You pay in advance so that you don’t have to deal with money on arrival.

Restaurant Reservations

• For top restaurants, places like Tickets in Barcelona or French Laundry in Napa, you’ll need to book in advance, like 4-6 months. So I’d say this may be the first thing to do when you’re considering a trip and a top restaurant is a must.
• For any other local restaurants, I’ll book these in usually the 1 week before or the week of a trip. I find that with a party of 2, it’s not always difficult to get a reservation.
• I try not to sweat over restaurants like I used to in the past as I’ve realized that when you’re in a new city, there’s usually a ton of options so I go in with a longer list than usual and pick out a few.

Experiences/Attractions

• If you’re keen to do a group tour, especially through Viator, I’d recommend booking 3-4 weeks in advance. If they’re a small group tour, these will definitely fill in, especially in the summer.
• For major sights like the Vatican or the Sagrada Familia, entry tickets should be book well in advance. I made the mistake of showing up at the Sagrada without a ticket and couldn’t get in that day.
• Decide your “must-see” list and book these in as soon as you know your itinerary. If you’re headed somewhere for an attraction, it’s better to play it safe.

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